Prince Harry, 31, took a well-deserved night off on Wednesday (Jan. 13) and let loose at a London shindig for socialite Anneke Gilkes. Princess Eugenie, the Duchess of Cambridge's brother, James Middleton, as was Holly Branson also attended the birthday bash.
Two names that stood out on the guest list, however, were presenter Natalie Pinkham and blond socialite Astrid Harbord. Both women have been linked to Harry in the past, when the prince was in his 20s.
Harry and Natalie, who is expecting her second baby with husband Owain Walbyoff, were first linked in the summer of 2006, after pictures surfaced of the pair enjoying a night out together.
At the time, reports claimed that Harry was "infatuated" with the sports presenter, although Natalie has always maintained that she is simply a friend.
Shortly after Harry split from his first long-term girlfriend Chelsy Davy in 2009, the prince was also briefly linked to Astrid, the daughter of late aristocrat Charles Harbord. Harry and Astrid, who now works in PR, were seen leaving a club together and climbing into a taxi.
Harry is known to remain on good terms with his former love interests. For his 30th birthday party, he invited two long-term ex-girlfriends, Cressida Bonas and Chelsy, to his celebrations.
His latest outing took the party-loving prince to Battersea's Bunga Bunga club to celebrate Anneke's birthday. Harry is particularly close to Anneke's husband, Charlie Gilkes, who co-owns the venue as well as other drinking spots Maggie's, Bart's and Mr. Fogg's in London.
Wearing a white shirt and navy trousers, Harry was seen making an exit at the end of the night, escorted by a couple of protection officers.
Harry and Charlie's friendship goes way back and in 2014 the prince attended Charlie and Anneke's wedding in Italy.